Digital transformation within vital societal functions has been going on for a long time. The aim has primarily been efficiency and cost savings, but also to make it easier for employees and for citizens who take advantage of the societal services. Digital transformation has many positive consequences, but also poses challenges. Studies and investigations have shown that, for example, rapid changes in technology, immature technology, lack of national coordination and insufficient customer competence mean that vulnerabilities are embedded into IT systems. These vulnerabilities can be exploited by antagonists in a gray zone or during a war, in order to destroy IT systems, manipulate data or spread disinformation. In this study, we have compiled problems with digital transformation that have been identified in previous FOI studies. We discuss how the nature of the problems change when the threat level changes from peace to gray zone or war, when the IT systems are being exposed to a greater degree to antagonistic attacks by a state actor or his agent. We also present 15 pitfalls that represent conditions that are functional in peacetime but create problems in a gray zone and war. The compilation of problems and pitfalls can serve as a basis for contingency planners within vital societal functions in the work of preparing activities to be able to continue even in gray zone and war.